Harmine hydrochloride

Names

[ CAS No. ]:
343-27-1

[ Name ]:
Harmine hydrochloride

[Synonym ]:
7-Methoxy-1-methyl-9H-β-carbolinhydrochlorid
7-Methoxy-1-methyl-9H-β-carboline hydrochloride
Harmine.HCL
EINECS 206-443-8
Harmine hydrochloride hydrate
Harmine monohydrochloride
MFCD00012641
9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl-, monohydrochloride
HARMINE HYDROCHLORIDE
7-Methoxy-1-methyl-9H-β-carboline hydrochloride (1:1)
7-Méthoxy-1-méthyl-9H-β-carboline chlorhydrate
9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl-, hydrochloride (1:1)
Banisterine Hydrochloride

Biological Activity

[Description]:

Harmine Hydrochloride (Telepathine Hydrochloride) is a natural dual-specificity tyrosine phosphorylation-regulated kinase (DYRK) inhibitor with anticancer and anti-inflammatory activities. Harmine has a high affinity of 5-HT2A serotonin receptor, with an Ki of 397 nM[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> DYRK

[Target]

Ki: 397 nM (5-HT2A serotonin receptor)[1], DYRK1A[2]

[In Vitro]

Harmine inhibits tau phosphorylation by DYRK1A by selected DANDYs, with an IC50 of 190 nM[2]. Harmine negatively regulates homologous recombination (HR) by interfering Rad51 recruitment, resulting in severe cytotoxicity in hepatoma cells. Furthermore, NHEJ inhibitor Nu7441 markedly sensitizes Hep3B cells to the anti-proliferative effects of Harmine[3].

[In Vivo]

It is shown that brain water content is significantly increased in the TBI group. Treatment with Harmine significantly reduces the tissue water content at 1, 3 and 5 days, compared with the TBI group. Harmine treatment significantly reduces the escape latency at 3 and 5 days, compared with the TBI group. Post-TBI administration of Harmine significantly improves the motor function recovery of the rats at 1, 3 and 5 days following TBI, compared with the TBI group without Harmine treatment. The neuronal survival rate in the Harmine-treated group is significantly increased, compared with the TBI group. Administration of Harmine results in marked elevation in the expression of GLT-1, compared with the TBI group. The administration of Harmine significantly reduces the expression of caspase 3, compared with the TBI group[4].

[References]

[1]. Glennon RA, et al. Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors. Drug Alcohol Depend. 2000 Aug 1;60(2):121-32.

[2]. Neumann F, et al. DYRK1A inhibition and cognitive rescue in a Down syndrome mouse model are induced by new fluoro-DANDY derivatives. Sci Rep. 2018 Feb 12;8(1):2859.

[3]. Zhang L, et al. Harmine suppresses homologous recombination repair and inhibits proliferation of hepatoma cells. Cancer Biol Ther. 2015;16(11):1585-92.

[4]. Zhong Z, et al. Treatment with harmine ameliorates functional impairment and neuronal death following traumatic brain injury. Mol Med Rep. 2015 Dec;12(6):7985-91.

Chemical & Physical Properties

[ Boiling Point ]:
421.4ºC at 760mmHg

[ Melting Point ]:
265-270°C

[ Molecular Formula ]:
C₁₃H₁₃ClN₂O

[ Molecular Weight ]:
248.708

[ Flash Point ]:
139.8ºC

[ Exact Mass ]:
248.071640

[ PSA ]:
37.91000

[ LogP ]:
3.83510

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MG9450000

CHEMICAL NAME :: Harmine, hydrochloride

CAS REGISTRY NUMBER :: 343-27-1

LAST UPDATED :: 199709

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C13-H12-N2-O.Cl-H

MOLECULAR WEIGHT :: 248.73

WISWESSER LINE NOTATION :: T B656 EN HMJ F1 KO1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 38 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 79,127,1943

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
1544

[ WGK Germany ]:
3

[ RTECS ]:
MG9450000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%